This paper seeks to answer if a rising India will repeat the pattern of all rising great powers since the Napoleonic times by attempting regional hegemony. This research deduces India's grand strategy of regional hegemony from historical and conceptual perspectives. The underlying assumption is that even though India has never consciously and deliberately pursued a grand strategy, its historical experience and geo-strategic environment have substantially conditioned its security behaviour and desired goals. To this extent, this research develops a theoretical framework to analyse grand strategy. This framework is then applied to five pan-Indian powers - the Mauryas, the Guptas, the Mughals, British India and the Republic of India - to understand their security behaviour.